Cottage Romance - Vacation Rentals in Montegrossi

Il Colombaio by VacaVilla From US $399
         

|
10.0 (2 Reviews)
Villa
  • Parking
  • Pool
  • View
Villa Gaia From US $1,189
         

New
Cottage
  • Air Conditioner
  • Parking
  • Pool
Villa Radda by MMega From US $799
         

10.0 (7 Reviews)
Villa
  • Air Conditioner
  • Pool
  • Private Pool

Luxury Places to Stay in Montegrossi

Over 364+ Luxury Places to Stay in or Near Montegrossi
Villa Vigneto Estate From US $13,260
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Chianti villa rental From US $5,657
         

New
Villa
  • Air Conditioner
  • Parking
  • Pool
Villa Radda - Florence Area From US $5,616
         

Villa Radda - Florence Area From US $4,661
         

Top-Rated Vacation Rentals with a Pool in Montegrossi

Over 279+ Top-Rated Vacation Rentals with a Pool in or Near Montegrossi
"La Casina delle Fate" a pretty little house in Tuscany From US $89
         

10.0 (69 Reviews)
House
  • Parking
  • Pool
  • Designated Smoking Area
Cavarchino B&B From US $187
         

10.0 (44 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Il Boschetto, Radda in Chianti, Siena and Chianti From US $347
         

10.0 (4 Reviews)
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool
Apartment Cortona From US $139
         

10.0 (4 Reviews)
Other
  • Parking
  • Pool
  • Designated Smoking Area
Villa Oliveta, Gaiole in Chianti, Siena and Chianti From US $434
         

Sestuccina From US $202
         

|
10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Montegrossi

Over 189+ Pet-Friendly Vacation Rentals in or Near Montegrossi
Casa Pieralli From US $100
         

9.0 (5 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Child Friendly
Tribolina by Interhome From US $128
         

9.8 (8 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Lovely home in Gaiole in Chianti SI From US $498
         

6.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Apartment Siena From US $227
         

10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Gittori, Gaiole in Chianti, Siena and Chianti From US $483
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in Montegrossi

Over 164+ Large Vacation Homes & Villas in or Near Montegrossi
Vertine Countryside From US $349
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lo Scoiattolo n° 10 by Interhome From US $340
         

9.0 (7 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool

Wheelchair Accessible Vacation Homes in Montegrossi

Over 10+ Wheelchair Accessible Vacation Homes in or Near Montegrossi
Casa Vacanze Chianti Summer From US $279
         

|
9.6 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Rocca di Castagnoli From US $197
         

9.2 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Holiday Apartment Chianti Summer From US $228
         

4.8 (6 Reviews)
Villa
  • Pet Friendly
  • Pool
  • Wheelchair Accessible
Le Lappe From US $489
         

|
9.3 (206 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Podere Erbolino From US $1,041
         

|
9.2 (21 Reviews)
Villa
  • Parking
  • Pet Friendly
  • View
Agri Resort La Forra From US $128
         

9.0 (104 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Castello Di Meleto From US $227
         

|
8.7 (682 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Montegrossi Vacation Rentals and Airbnb Places to Stay Under $200

Over 137+ Montegrossi Vacation Rentals and Airbnb Places to Stay Under $200
La stalla From US $149
         

8.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Pool
L' Eroico From US $195
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Adorable house in charming Chianti hamlet btwn Siena, Arezzo and Florence From US $191
         

La Farfalla n°5 by Interhome From US $150
         

9.0 (4 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool
La Colomba n°4 by Interhome From US $158
         

9.0 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool
Il Ghiro n°8 by Interhome From US $148
         

9.0 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool

Instantly Bookable Vacation Homes in Montegrossi

Over 147+ Instantly Bookable Vacation Homes in or Near Montegrossi
Podere Vecciale' estate From US $622
         

New
Other
  • Pool
  • Private Pool
  • Balcony/Terrace
Cerbiatto n°5A by Interhome From US $73
         

8.8 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Il Pettirosso n°7 by Interhome From US $130
         

8.0 (3 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Pool

About Montegrossi Vacation Rentals

With more than 156 Montegrossi vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Cottageromance and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Montegrossi.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cottageromance Montegrossi, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Montegrossi. Places to stay near Montegrossi are 2109.99 ft² on average, with prices averaging $1,027 a night.

Cottageromance makes it easy and safe to find and compare vacation rentals in Montegrossi with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Montegrossi

Type Count
Villas 145
Cottages 8
Hotels with Suites 1
Vacation Homes 1
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Montegrossi

Pro Tip: Cottageromance makes it easy to compare the best listings on Cottageromance homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cottageromance homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Montegrossi.

Weather in Montegrossi

View the weather forecast for Montegrossi before booking your Montegrossi Vacation Rentals to confirm your best time to go.

December - February
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Complexes around Montegrossi, IT


Montegrossi Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Montegrossi?
How many vacation rentals are available in Montegrossi?

Currently, the total number of properties listed in 2026 is over 156 in the Montegrossi area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Montegrossi.